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Middlemass v. United States

United States District Court, D. Connecticut

March 28, 2016



Janet C. Hall United States District Judge


Craig Middlemass (“Middlemass”) brings this Motion to Vacate, Set Aside, or Correct Sentence under section 2255 of title 28 of the United States Code. See Motion to Vacate, Set Aside, or Correct Sentence (the “Motion” or the “Section 2255 Motion”) (Doc. No. 1). His first contention is that his sentence violated the Ex Post Facto Clause of the Sixth Amendment to the United States Constitution because it applied a version of the Guidelines that came into effect after the commission of the crime of conviction, and that was more punitive than the version of the Guidelines in effect during the commission of his crime of conviction. See U.S.S.G. § 1B1.11(b)(1). His second contention is that his counsel was ineffective, in violation of the Assistance of Counsel Clause of the Sixth Amendment to the United States Constitution, for failing to appeal his sentence when asked.

The United States has opposed the Motion. See Memorandum in Opposition (“Opposition”) (Doc. No. 7). For the reasons set forth below, the Motion is DENIED.


A. Middlemass’s Plea and Sentencing

On May 2, 2007, Craig Middlemass waived his right to an indictment and pled guilty to an Information charging him with one count of Production of Child Pornography, in violation of section 2251(a) of title 18 of the United States Code. See Minute Entry (Doc. No. 19). The Information alleged, and the Plea Agreement stipulated to, conduct comprising the offense of conviction that spanned from the summer of 2003, when Middlemass induced an individual known as Minor A to take part in the production of sexually explicit photographs in California, through some time in 2004, when Middlemass physically transported those images in interstate commerce to Connecticut. See Information (Doc. No. 15) at 1, and Plea Agreement (Doc. No. 17) at 10.[1] The Guidelines provide that, in determining which version applies for purposes of the Ex Post Facto clause, “the last date of the offense of conviction is the controlling date.” U.S.S.G. § 1B1.11, comment. (n.2).

The Plea Agreement also stipulated to facts establishing that Middlemass possessed more than 3, 200 images of child pornography, in the form of photographs, 8mm and 16mm films, compact discs, digital video discs, computer diskettes, magazines, books, buttons, personal photo albums, and digital images stored on his computers’ hard drives. Id. Some of these images portrayed sadistic or masochistic conduct. Id. at 5. Further, the Plea Agreement stipulated that Middlemass had distributed at least nine images “[a]t various times between 2003 and 2006.” Id. at 10-11.

The Plea Agreement further stipulated to a Guidelines range of 262 to 327 months. Id. at 4. Though the Agreement does not expressly state which version of the Guidelines it applies, section 1B1.11(a) of the Guidelines would normally mandate that the version in effect at sentencing would apply. Consequently, the Agreement is likely to have applied the 2006 version of the Guidelines, [2] and this is the version that the court presumably applied at Middlemass’s sentencing on October 26, 2007. At that proceeding, Middlemass was sentenced to the top of the 2006 Guidelines range: 327 months. See Case No. 07-CR-91, Judgment (Doc. No. 35). As sentence was imposed, the court stated, “I think that the Guidelines are appropriate. The top of the Guideline is appropriate. As a matter of fact, I wouldn’t be surprised if I felt 30 years is appropriate. I think this is a very serious matter.” Case No. 07-CR-91, Sentencing Transcript (10/26/2007) (Doc. No. 36) at 36:6-11.

According to his Motion, Middlemass asked his counsel to appeal the sentence and his counsel failed to do so. Section 2255 Motion at 5. Middlemass explains, in his Reply to the United States’ Opposition, that at some point after his sentencing, he learned that his attorney had contacted Middlemass’s brother to explain that “the Judge’s offer [to permit an appeal notwithstanding his Plea Agreement’s waiver of such right] was a mere formality and that if there was an appeal to be made, he would have already made it.” Reply to Response to Motion (“Reply to Response”) (Doc. No. 11) at 24.

B. Changes to the Guidelines

At the time Middlemass engaged in the conduct giving rise to his offense of conviction, i.e. from 2003 to October 31, 2004, [3] the United States Sentencing Guideline that governed Middlemass’s offense mandated a Base Offense Level of 27 and contained a single applicable enhancement of two points to account for the fact that Minor A, Middlemass’s victim, was between the ages of 12 and 16 at the time of the offense. See U.S.S.G. § 2G2.1 (2003). After subtracting the three points Middlemass was granted for acceptance of responsibility under section 3E1.1, the 2003 Guidelines would have mandated an Offense Level of 26, which, considering Middlemass’s Criminal History Category of I, would result in a sentencing range of 63 to 78 months.

Just as they do today, the 2003 Guidelines also required the imposition of a criminal statute’s mandatory minimum sentence if such mandatory minimum “is greater than the maximum of the applicable guideline range.” 2003 U.S.S.G. § 5G1.1(b). The mandatory minimum penalty for the crime of which Middlemass was convicted was, at the time he committed it and today, fifteen years’ imprisonment. 18 U.S.C. § 2251(a) (2003). Thus, Middlemass’s Guidelines range under the 2003 version of the Guidelines was 180 months.

However, the Guidelines changed considerably on November 1, 2004. The Base Offense Level for the offense of conviction was raised to 32 from 27, and several new enhancements were added. Those that Middlemass stipulated applied to his case were a two-point enhancement for contact with the victim; a two-point enhancement for involvement with distribution; and a four-point enhancement for material that “portrays sadistic or masochistic conduct or other depictions of violence.” Guidelines § 2G2.1 (2004). After accounting for Middlemass’s three-point reduction for acceptance of ...

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